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Polybetaine fluorescent labeling agent and preparation method thereof

A fluorescent labeling and betaine technology, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of complicated purification processing, low labeling efficiency, expensive raw materials, etc., and achieves high fluorescence brightness, environment-responsive type, and high reaction yield. Effect

Inactive Publication Date: 2013-02-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Most of the existing methods for fluorescently labeling water-soluble responsive polymers require the use of expensive functionalized polymer precursors or the synthesis of fluorescent free radical initiators and chain transfer agents, which have complex steps and expensive raw materials ( Many dyes with functional groups need to be imported), low labeling efficiency and difficult to control, low yield, complicated and incomplete purification after labeling, etc.

Method used

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  • Polybetaine fluorescent labeling agent and preparation method thereof
  • Polybetaine fluorescent labeling agent and preparation method thereof
  • Polybetaine fluorescent labeling agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The betaine monomer is N-(3-sulfopropyl)-N-(1-methacrylic acid ethyl)-N,N-dimethylammonium, the structural formula is:

[0057]

[0058] The FR group of the copolymerized fluorescent monomer is rhodamine B, abbreviated as RB-MA, and the structural formula is:

[0059]

[0060] 1g of betaine monomer is dissolved in potassium dihydrogen phosphate-disodium hydrogen phosphate buffered aqueous solution with a pH of 7.0, and the monomer concentration is 0.6mol L -1 , adjust the concentration of NaBr to 0.50mol L -1 , the required amount of RB-MA, chain transfer agent (CTA, S-isocyanate-N-ethyl-N'-phenyl dithiocarbamate) and initiator (V-501, azo Dicyanovaleric acid) was dissolved in 0.5mL methanol, the two were mixed, and the reaction molar ratio was: betaine monomer: [CTA]: [V-501]: [RB-MA]=1600:1:0.2 :2.4. Liquid nitrogen was used for three freeze-thaw cycles to completely remove residual oxygen, and then the reaction was stirred at 70° C. for 10 hours; the reactio...

Embodiment 2

[0065] Betaine monomer is N-(3-sulfopropyl)-N-(1-methacrylamidoethyl)-N,N-methylammonium, the structural formula is:

[0066] The FR group of the copolymerized fluorescent monomer is rhodamine 6G, abbreviated as R6G-MA, and the structural formula is:

[0067]

[0068] 1g of betaine monomer is dissolved in potassium dihydrogen phosphate-disodium hydrogen phosphate buffer solution with a pH of 6.5, and the monomer concentration is 1.0mol L -1 , adjust the concentration of NaBr to 0.50mol L -1 , the required amount of copolymerized fluorescent monomer, chain transfer agent (CTA, S-isocyanate-N-ethyl-N'-phenyl dithiocarbamate) and initiator (V-501, even Azodicyanovaleric acid) was dissolved in 0.5mL methanol, and the two solutions were mixed, and the reaction molar ratio was: betaine monomer:[CTA]:[V-501]:copolymerized fluorescent monomer=1000:1: 0.15:2.0. Three freeze-thaw cycles with liquid nitrogen were used to completely remove residual oxygen, and then the reaction wa...

Embodiment 3

[0073] The betaine monomer is N-(3-carboxylic acid ethyl)-N-(1-methacrylic acid ethyl)-N,N-dimethylammonium, the structural formula is:

[0074]

[0075] The FR group of the copolymerized fluorescent monomer is rhodamine B, abbreviated as RB-MA, and the structural formula is:

[0076]

[0077] 1g of betaine monomer is dissolved in potassium dihydrogen phosphate-disodium hydrogen phosphate buffered aqueous solution with a pH of 7.0, and the monomer concentration is 1.0mol L -1 , adjust the concentration of NaBr to 0.50mol L -1 , the required amount of copolymerized fluorescent monomer, chain transfer agent (CTA, S-isocyanate-N-ethyl-N'-phenyl dithiocarbamate) and initiator (V-501, even Azodicyanovaleric acid) was dissolved in 0.5mL methanol, and the two solutions were mixed, and the molar ratio of the reaction feed was: betaine monomer:[CTA]:[V-501]:copolymerized fluorescent monomer=200:1: 0.25:1.0. Liquid nitrogen was used for three freeze-thaw cycles to completely re...

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Abstract

The invention discloses a polybetaine fluorescent labeling agent and a preparation method thereof. The polybetaine fluorescent labeling agent is shown as a formula I, wherein R1 is hydrogen or methyl; R2 is carboxyl or sulfo group; R3 is hydrogen or methyl; FR is an organic conjugate fluorophore, X is O or NH; Y is O or NH; m is a natural number within 1-3; n is a natural number within 1-6, p is a natural number within 2-4; q2 is a number within 0.1-10; and q1+q2 is a number within 50-2000. The fluorescent labeling method of the polybetaine provided by the invention is completed in water solution, the stress on environmental pollution by using organic reaction media is reduced and the requirements on environmental protection and sustainable development are satisfied; the fluorescently-labeled polybetaine reagent is prepared through RAFT (reversible addition-fragmentation chain transfer ) controllable radical polymerization reaction in one step, the reaction step is simple, the reaction recovery rate is high and is more than 95 percent and 98 percent of fluorescent impurity molecules can be removed through a simple purification step; the large-scale production is easy to realize and the cost is reduced; and the fluorescent labeling reagent prepared by adopting the method has the advantages of high water solubility, environmental response, high fluorescent brightness and high light-emitting stability.

Description

technical field [0001] The invention relates to a fluorescent labeling agent and a preparation method thereof, in particular to a polybetaine fluorescent labeling agent and a preparation method thereof. Background technique [0002] Smart polymers are a large class of polymers that can respond specifically to various external environmental stimuli (including temperature, ionic strength, pH value, light radiation, electric field, magnetic field, and force field, etc.), and can be widely used as new functional materials all aspects of the national economy. Fluorescent labeling of responsive polymers is to introduce fluorescent groups into polymer chains, which can make polymers exhibit dual or multiple response characteristics, and facilitate the study of polymer response mechanisms and functions with the help of rich fluorescence analysis techniques properties, in-depth understanding of its structure-performance relationship, and then provide a theoretical basis for the desi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C08F220/38C08F220/60C08F220/36C08F2/38
Inventor 王飞赵江杨京法
Owner INST OF CHEM CHINESE ACAD OF SCI
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